3-乙基戊二酸酐 | 43080-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 3-乙基戊二酸酐
• 英文名称: 3-ethylglutaric anhydride
• 英文别名: 3-Ethylglutarsaeureanhydrid；4-Ethyloxane-2,6-dione
• CAS: 43080-12-2
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: YIEQRBOBYGITMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  258.2±9.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-乙基戊二酸酐 在 4-二甲氨基吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (1'SR,3RS)-1-(1'-naphthyl)ethyl methyl 3-ethylpentanedioate
  参考文献：
  名称：

  Prochiral recognition in the reaction of 3-substituted glutaric anhydrides with chiral secondary alcohols

  摘要：

  The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated. Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtain the corresponding diesters 16-20. The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, with the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively. The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.

  DOI：

  10.1021/jo00053a027
• 作为产物：
  描述：

  3-ethylglutaric acid 在 乙酰氯 作用下， 以96%的产率得到3-乙基戊二酸酐
  参考文献：
  名称：

  Unidirectional Dieckmann cyclizations on a solid phase and in solution

  摘要：

  DOI：

  10.1021/jo01304a015

文献信息

• Small molecules for treatment of hypercholesterolemia and related diseases
  申请人：Sircar C. Jagadish

  公开号：US20050277690A1

  公开（公告）日：2005-12-15

  The present invention provides compositions adapted to enhance reverse cholesterol transport in mammals. The compositions are suitable for oral delivery and useful in the treatment and/or prevention of hypercholesterolemia, atherosclerosis and associated cardiovascular diseases.

  本发明提供了适用于增强哺乳动物体内逆向胆固醇转运的组合物。这些组合物适合口服给药，并可用于治疗和/或预防高胆固醇血症、动脉粥样硬化及相关心血管疾病。
• Highly Enantioselective Thiolysis of Prochiral Cyclic Anhydrides Catalyzed by Amino Alcohol Bifunctional Organocatalysts and Its Application to the Synthesis of Pregabalin
  作者：Hong-Jun Yang、Fang-Jun Xiong、Xiao-Fei Chen、Fen-Er Chen

  DOI：10.1002/ejoc.201300464

  日期：2013.7

  Asymmetric thiolysis of prochiral cyclic anhydrides was achieved with our developed chiral sulfonamide and squaramide bifunctional organocatalysts based on amino alcohol scaffolds. The corresponding thioesters were obtained in high yields with excellent enantioselectivities. The usefulness of this methodology was demonstrated in the enantioselective synthesis of pregabalin.

  我们开发的基于氨基醇支架的手性磺酰胺和方酸酰胺双功能有机催化剂实现了前手性环酐的不对称硫解。相应的硫酯以高产率获得，具有优异的对映选择性。这种方法的实用性在普瑞巴林的对映选择性合成中得到了证明。
• Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of<i>meso</i>Cyclic Anhydrides
  作者：Lin-Jie Yan、Hai-Feng Wang、Wen-Xue Chen、Yuan Tao、Kai-Jun Jin、Fen-Er Chen

  DOI：10.1002/cctc.201600228

  日期：2016.7.6

  chloramphenicol‐base‐derived thiourea organocatalysts, (1S,2R)‐12 a–f and (1R,2R)‐15 a–c, and their use in the enantioselective alcoholysis of meso‐anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)‐12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)‐15 a–c. This technique was used to synthesize (R)‐(−)‐baclofen

  新的氯霉素基硫脲有机催化剂（1 S，2 R）-12 a - f和（1 R，2 R）15 a - c的合成及其在介孔酸酐的对映选择性醇解中的应用描述。特别是，如果使用低负荷的（1 S，2 R）-12 a – f负载，半酯具有出色的对映选择性。使用（1 R，2 R）‐ 15 a – c几乎没有达到对映选择性。该技术用于合成（R）-（-）-baclofen。
• Asymmetric ring opening of cyclic acid anhydrides with lipase in organic solvents
  作者：Kazuyoshi Yamamoto、Takaaki Nishioka、Jun'ichi Oda、Yukio Yamamoto

  DOI：10.1016/s0040-4039(00)82026-2

  日期：——

  A lipase (Amano P) catalyzed the asymmetric ring opening of 3-substituted glutaric anhydride with 1-butanol to afford the half esters having 60–91%ee.

  脂肪酶（Amano P）催化3-取代的戊二酸酐与1-丁醇的不对称开环，得到具有60-91％ee的半酯。
• Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of<i>meso</i>-cyclic anhydrides
  作者：Lingjun Xu、Shuwen Han、Linjie Yan、Haifeng Wang、Haihui Peng、Fener Chen

  DOI：10.3762/bjoc.14.19

  日期：——

  possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

  研发了一系列新型的氯霉素基础酰胺有机催化剂，它们在C-1位置具有NH官能团作为单齿氢键供体，并评估了其对中环酸酐的对映选择性有机催化醇解作用。发现这些结构多样的有机催化剂在酸酐的醇解中诱导高对映选择性，并成功地用于（S）-GABOB的不对称合成。